Head of Sales

The Opportunity We're looking for a Head of Sales - initially a player-coach who will build and scale our go-to-market while personally landing and managing strategic accounts. This is a rare opportunity to shape the go-to-market strategy of a fast-growing proptech startup and grow into full ownership of our GTM within 6-12 months. You'll work directly with our CEO, leading our sales and partnership team while also rolling up your sleeves to close strategic deals with lenders, brokerages, and proptech partners. What You'll Do Player (30% - Your Book of Business): Personally prospect, pitch, and close strategic accounts Build and execute account plans for high-volume institutional partnerships Drive significant growth from your strategic accounts Coach (70% - Building the Engine): Lead and coach a high-performing sales team focused on partner acquisition and growth Build and refine our account-based sales motion - getting management buy-in, enabling agents, driving adoption Develop sales processes and playbooks that work (even if imperfect - we value progress over perfection) Co-develop and execute on sales targets and hiring plans Scale the team strategically as we hit milestones and growth targets Hire and successfully onboard additional team members as we expand What Success Looks Like: Team performance: Build an engaged, productive team that consistently hits targets Revenue growth: Drive aggressive month-over-month growth in files processed through your team and strategic accounts Strategic account wins: Land and activate high-volume institutional partnerships. Execute account-based plans with measurable adoption across agent networks Process & systems: Establish repeatable, scalable sales processes and playbooks Who You Are Must-Haves: You are an experienced, hands-on builder - You’ve built sales motions, playbooks, GTM motions and systems to scale growth. You’re very comfortable with ambiguity and the unknown. If you’ve only been in roles where the process, systems, and playbook were mature and defined, this role likely isn’t for you. You are self-sufficient and extremely resourceful and excel without an infrastructure of people and resources around you. Ideal candidate has been a founding AE, or founding sales manager at a startup who demonstrated going from founder-led GTM to a scalable sales motion. 5-7+ years in partnership or channel sales GTM motion (where adoption is the key metric) - you understand the motion from top-down buy-in → enablement → adoption → retention and have been a key part of this flywheel motion. Demonstrated leadership experience - with or even without a formal title, you've coached teammates, built processes, helped with hiring/onboarding, understood budgets and plans. You lead by example and earn your stripes from the trenches. High-gravity relationship builder - personable, strong networker, comfortable in boardrooms and in the trenches Critical thinker with high curiosity - you ask smart questions, challenge assumptions, and solve problems creatively Ideally GTA based and excited about hybrid work (building team culture matters to us) Nice-to-Haves: Knowledge of real estate, mortgage, lending, or fintech industries (and better yet, a network in these spaces) Experience selling through associations or industry groups Track record working with distributed partner networks (agents, brokers, referral partners) Previous experience at a high-growth proptech, fintech, or legal tech company What We Offer Ownership & Growth: This role evolves into full GTM ownership within 6-12 months Clear Path: You'll work directly with the CEO with a roadmap to VP Sales/Head of Sales Player-Coach Comp:base/variable split - earn personal commissions on your strategic accounts, plus team-based incentives Equity: Meaningful equity stake in a growing proptech company Impact: You're not just filling a role - you're building the sales engine from the ground up Hybrid Flexibility: Work from our Toronto office and remotely as needed Ready to Build With Us? If you're a relationship-driven sales leader who wants to own the GTM strategy of a fast-growing proptech startup, we want to hear from you. #J-18808-Ljbffr